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  • Biological Diversity from a Structurally Diverse Library: Systematically Scanning Conformational Space Using a Pyranose Scaffold

    Author(s)
    Abbenante, Giovanni
    Becker, Bernd
    Blanc, Sebastien
    Clark, Chris
    Condie, Glenn
    Fraser, Graeme
    Grathwohl, Matthias
    Halliday, Judy
    Henderson, Senka
    Lam, Ann
    Liu, Ligong
    Mann, Maretta
    Muldoon, Craig
    Pearson, Andrew
    Premraj, Rajaratnam
    Ramsdale, Trade
    Rossetti, Tony
    Schafer, Karl
    Le Thanh, Giang
    Tometzki, Gerald
    Vari, Frank
    Verquin, Geraldine
    Waanders, Jennifer
    West, Michael
    Wimmer, Norbert
    Yau, Annika
    Zuegg, Johannes
    Meutermans, Wim
    Griffith University Author(s)
    Pearson, Andrew G.
    Year published
    2010
    Metadata
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    Abstract
    Success in discovering bioactive peptide mimetics is often limited by the difficulties in correctly transposing known binding elements of the active peptide onto a small and metabolically more stable scaffold while maintaining bioactivity. Here we describe a scanning approach using a library of pyranose-based peptidomimetics that is structurally diverse in a systematic manner, designed to cover all possible conformations of tripeptide motifs containing two aromatic groups and one positive charge. Structural diversity was achieved by efficient selection of various chemoforms, characterized by a choice of pyranose scaffold of ...
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    Success in discovering bioactive peptide mimetics is often limited by the difficulties in correctly transposing known binding elements of the active peptide onto a small and metabolically more stable scaffold while maintaining bioactivity. Here we describe a scanning approach using a library of pyranose-based peptidomimetics that is structurally diverse in a systematic manner, designed to cover all possible conformations of tripeptide motifs containing two aromatic groups and one positive charge. Structural diversity was achieved by efficient selection of various chemoforms, characterized by a choice of pyranose scaffold of defined chirality and substitution pattern. A systematic scanning library of 490 compounds was thus designed, produced, and screened in vitro for activity at the somatostatin (sst1-5) and melanin-concentrating hormone (MCH1) receptors. Bioactive compounds were found for each target, with specific chemoform preferences identified in each case, which can be used to guide follow-on drug discovery projects without the need for scaffold hopping.
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    Journal Title
    Journal of Medicinal Chemistry
    Volume
    53
    Issue
    15
    DOI
    https://doi.org/10.1021/jm1002777
    Copyright Statement
    Self-archiving of the author-manuscript version is not yet supported by this journal. Please refer to the journal link for access to the definitive, published version or contact the authors for more information.
    Subject
    Medicinal and biomolecular chemistry
    Biomolecular modelling and design
    Cheminformatics and quantitative structure-activity relationships
    Organic chemistry
    Organic chemical synthesis
    Pharmacology and pharmaceutical sciences
    Publication URI
    http://hdl.handle.net/10072/35867
    Collection
    • Journal articles

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